Woodstock Vacations from $324

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Your Woodstock Vacation

Our Woodstock vacation packages allow you to create your own adventure. Tailor your getaway to your style and interests and make every moment count in this wonderful city. Fill up your itinerary with visits to Shenandoah County Fairgrounds, Woodstock Museum and Shenandoah Vineyards, some of the top attractions you shouldn't miss during a trip to Woodstock. Stop daydreaming and start adventuring. Browse the many options on Expedia today and finally put your Woodstock vacation plans into gear!

The Latest Woodstock Vacation Packages

Prices and availability subject to change. Additional terms may apply.
Residence Inn by Marriott - Silver Spring

Residence Inn by Marriott - Silver Spring

3 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 9
Roundtrip non-stop flight included
Los Angeles (LAX) to Baltimore (BWI)
9/10 Wonderful! (441 reviews)
We had a wonderful stay and the breakfast was good. The guests were really noisy (Fri and Sat night). Otherwise, a great place to stay and it was convenient.

Reviewed on Apr 14, 2024

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 9 - Jul 16
Roundtrip non-stop flight included
Los Angeles (LAX) to Washington (DCA)
8.6/10 Excellent! (1,012 reviews)
The Desk Staff was welcoming and knowledgable. Valet Service was courteous responsive.

Reviewed on Apr 17, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
May 25 - May 27
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,952 reviews)
I stayed for 3 days, never had housekeeping come. I asked for towel, the man had an attitude with me. Otherwise the place was great. I always tip housekeeping, not this time

Reviewed on Apr 24, 2024

Ulysses

Ulysses

3 out of 5
Midtown
Save 100% on your flight
per person
Jun 5 - Jun 8
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (332 reviews)
I loved this hotel! My husband and I did an east coast trip by train and we got there at night. We were able to walk from the station to the hotel no problem. The hotel itself is so beautiful. The decor really was incredible down to every detail. The staff was so kind and helpful as well. They also have bars in the lobby area. We went to Blooms on Tuesday night for the jazz band which was so great. I had espresso martinis and they were delicious. I loved everything about our stay! I’m a big fan of boutique hotels and Hotel Ulysses just went to the top of my list.

Reviewed on Apr 23, 2024

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
per person
Jun 5 - Jun 8
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.4/10 Exceptional! (891 reviews)
The rooms and decor are excellent. The staff are friendly.

Reviewed on Mar 15, 2024

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
5,200
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Shenandoah River State Park, Shenandoah Vineyards and Cave Ridge Vineyard

Woodstock Hotel Deals

Hampton Inn & Suites Woodstock, VA
Hampton Inn & Suites Woodstock, VA
2.5 out of 5
1150 Motel Dr, Woodstock, VA
Fully refundableReserve now, pay when you stay
The price is $121 per night from May 19 to May 20
$121
$133 total
includes taxes & fees
May 19 - May 20
8.8/10 Excellent! (1,000 reviews)
"Great location for easy access to the interstate."

Reviewed on Apr 13, 2024

Hampton Inn & Suites Woodstock, VA
Comfort Inn Woodstock Shenandoah
Comfort Inn Woodstock Shenandoah
2.5 out of 5
1011 Motel Dr, Woodstock, VA
Fully refundableReserve now, pay when you stay
The price is $97 per night from May 19 to May 20
$97
$107 total
includes taxes & fees
May 19 - May 20
8.6/10 Excellent! (790 reviews)
"Nice location great staff"

Reviewed on Apr 22, 2024

Comfort Inn Woodstock Shenandoah
Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
2.5 out of 5
1130 Motel Dr, Woodstock, VA
Fully refundable
The price is $114 per night from May 19 to May 20
$114
$126 total
includes taxes & fees
May 19 - May 20
8.8/10 Excellent! (1,004 reviews)
"Nice stay.."

Reviewed on Apr 20, 2024

Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
See all 1,023 properties in Woodstock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Explore other types of vacation packages

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All Inclusive Vacations

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Frequently asked questions

How much does a Woodstock vacation package cost?
Our Woodstock vacation packages, which begin from just $324, are an ideal way to save money. All you have to do is choose your preferred hotels, flights and rental car to create your dream escape.
How do I get a cheap travel package to Woodstock?
Combining your flight and hotel with Expedia won’t just save valuable time — it’ll save you a tidy sum too. A Woodstock vacation package makes it a cinch to organize your dream adventure. With more than 550 airlines all over the world to select from, finding flights that fit your busy schedule won’t be a hassle. On top of that, we have over 1,000,000 properties globally to choose from. Now that’s what you call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Woodstock?
With lots to discover in Woodstock, it’s a good idea to lock in a hotel near its attractions. Shenandoah County Fairgrounds, Woodstock Museum and Seven Bends State Park are some fascinating ones to add to your to-do list.
What are the top hotels in Woodstock?
Get your vacation off to an excellent start by reserving a room at Comfort Inn Woodstock Shenandoah. It’s one of most sought-after properties in Woodstock. Another cozy option is Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel.
How far in advance should I book my Woodstock vacation?
Travelers are normally able to compare international fares on Expedia up to a year in advance of departure. Booking late? With a little bit of luck, it’s still possible to score a cheaper ticket just weeks before your journey.
What does an Expedia Woodstock travel package include?
You can select from a combination of flights, hotels and rental cars. Once you’ve made your booking, you can add some experiences and activities. Want to pick your airfare class? That’s also easy to do. The choice is yours when it comes to putting together your perfect Woodstock escape.
What should I know before booking a Woodstock travel package?
A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever your vacation goals are, there’s sure to be a package that suits your budget.
Can I choose my airline with a Woodstock Expedia vacation package?
With a vacation package, you’re the boss. Whether you’d like to fly to Woodstock in first class or coach, simply pick from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Woodstock vacation package?
Whether it’s your hotel or flight, yes, you can cancel or amend it. Locked in your Woodstock vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For older bookings, you may incur a fee from your hotel, airline or car rental company. For more details, visit our Customer Service Portal. We’re here to help you every step of the way.

Discover the most popular places to visit in Woodstock

Image for Shenandoah County Fairgrounds

Shenandoah County Fairgrounds

4.5/5(23 reviews)

Take the family on an outing to Shenandoah County Fairgrounds during your trip to Woodstock. While you're here, you can savor the top-notch restaurants.

Shenandoah County Fairgrounds
Image for Woodstock Tower Observation Site

Woodstock Tower Observation Site

You can find out about the history of Woodstock with a visit to Woodstock Tower Observation Site. While in this vibrant area, you can savor the top-notch restaurants.

Woodstock Tower Observation Site
Image for Woodstock Museum

Woodstock Museum

5/5(1 review)

You can enjoy some culture when you stop by Woodstock Museum in Woodstock. While you're here, you can savor the top-notch restaurants.

Woodstock Museum

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.